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Check availability on Chestertown Gay-Friendly Hotels

Our top choices for Chestertown LGBT-friendly hotels

Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (80 reviews)
"clean, comfortable, and staff was friendly and helpful. "
United States
Gail
The price is ₹12,142
₹13,882 total
includes taxes & fees
18 May - 19 May
The Lodge at Great Oak Landing
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (440 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is ₹6,811
₹7,560 total
includes taxes & fees
14 May - 15 May
Red Roof Inn & Suites Chestertown
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (909 reviews)
"Great visit"
United States
Danielle
The price is ₹10,854
₹12,047 total
includes taxes & fees
25 May - 26 May
Comfort Inn & Suites Chestertown
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (543 reviews)
"Breakfast menu was very good, staff friendly and helpful. "
United States
JoEllen
The price is ₹13,769
₹15,421 total
includes taxes & fees
14 May - 15 May
Vandiver Inn
Lobby

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (642 reviews)
"Very good breakfast. Nice selection to choose from. "
United States
Charlotte
The price is ₹8,922
₹9,993 total
includes taxes & fees
18 May - 19 May
Hampton Inn & Suites Baltimore/Aberdeen
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"Great location. Beautiful room and exemplary service. "
United States
Nathan
The price is ₹21,497
₹24,507 total
includes taxes & fees
10 May - 11 May
Flag House Inn
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,003 reviews)
"We were very pleased with our overnight here - it was economical and more than sufficient. It was clean, comfortable and it was nice to have breakfast included (try the cinnamon buns!) "
United States
Susan
The price is ₹12,678
₹14,073 total
includes taxes & fees
10 May - 11 May
Holiday Inn Express Annapolis East-Kent Island by IHG
Restaurant

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (228 reviews)
"Room were very clean, staff were excellent and friendly and helpful!"
United States
Matthew
The price is ₹8,829
₹9,888 total
includes taxes & fees
25 May - 26 May
Courtyard Aberdeen at Ripken Stadium
Terrace/patio

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (370 reviews)
"Rooms clean and spacious. Breakfast was better than any other hotel I've stayed at. Staff friendly and helpful. Had everything you could want in a hotel. Would recommend to friends and family. "
United States
Jeanette
The price is ₹9,232
₹10,340 total
includes taxes & fees
18 May - 19 May
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (337 reviews)
"The staff was lovely and so accommodating. Definitely the best part of our stay."
United States
Maritza
The price is ₹10,432
₹11,684 total
includes taxes & fees
10 May - 11 May
Fairfield Inn & Suites by Marriott Aberdeen
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Frequently asked questions

Searching for an LGBTQ-friendly hotel in Chestertown?
Whether you are travelling with your partner or flying solo, you'll find Chestertown hotels that are members of the International Gay & Lesbian Travel Association on Expedia. Discover the people, places and traditions found only in Chestertown.
What is the top LGBTQ-friendly place to stay in Chestertown?
Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing are other good options for your stay.
How many LGBTQ-friendly hotels will I find in Chestertown?
There are currently 3 LGBTQ-friendly hotels in Chestertown.
What should I do while I'm visiting Chestertown?
During your trip, get out and enjoy everything Chestertown has to offer. You and your travelling companions may want to visit Northern Chesapeake Bay, Chesapeake Bay and Historical Society of Kent County Maryland. While you're here, create some great memories of your trip with stops at Garfield Center for the Arts at the Prince Theater, Chestertown Historic District and Rolphs Wharf Marina.
What is a gay-friendly hotel in Chestertown?
LGBTQ-friendly hotels are places where lesbian, gay, bisexual and transgender travellers are proudly welcomed. Expedia has worked with the International Gay and Lesbian Travel Association (IGLTA) to compile a selection of LGBTQ-friendly hotels worldwide. In Chestertown, hotels affiliated with IGLTA prioritise a diverse environment in which guests are welcomed, respected and not obliged to declare or hide their sexual orientation.
What can I expect from LGBTQ-friendly accommodation in Chestertown?
Take a holiday from the ordinary; stay at a gay-friendly hotel in Chestertown, and the staff will help you explore the local gay scene and the LGBTQ+ culture. Many of our LGBTQ-friendly accommodation options offer community-specific packages, exclusive tours and opportunities for social interaction.

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